The First Time
by secretffw
Summary: "Look, I know you hate me. I was in love with Blair and I'm sorry". Chuck's words to Nate at Lily and Bart's wedding. When and how did Chuck realise what he really felt?
1. Chapter 1

A/N: I wrote a short and extended version of the story. I just couldn't decide which one I preferred. Chapter 1 is the short version and chapter 2 the more detailed version. Pick whichever one you like.

Tonight was just like any other. A woman hooking on to his facade of attentiveness and then being reeled in by his witty and seductive conversation and subtle physical advances. The final landing was never difficult and often had been dead certain from the first moment of eye contact.

Here she was, the same as so many others before. Her childish brown curls swishing around as she straddled him on the bed. A silly headband failing to have any control, clearly just a lame accessory used to draw attention to her plain self. Her oddly small hands just followed the usual pathway. Up to his chest, grabbing his shoulders, running back down to his belt, a boring 'will she-won't she' as her fingers slide under his waist band but then out of it again and again.

She should put a bit more effort into kissing him effectively. He should not have to try to stay hard. His own hands performed the same show as so many times before. Politely starting on the back of her thighs just above the knee. Pretending every centimetre climbed towards her centre excited him more and more so that she would be encouraged. It didn't really. Her skin felt scratchy under his finger tips and the lace of her French knickers cheap once he reached them.

Now she was doing that thing at the base of his neck that women seemed to think he would enjoy. Tickling him a bit and tangling her finger tips into the hair there. If he had been looking for a head massage he would have gone somewhere authentic to ensure a decent experience.

He flipped her down into the mattress in an attempt to speed things along a bit. He could probably get out of here in the next 20 minutes if he took control now. He mentally referred to his extensive toolkit of moves and techniques to hurry things along. Hopefully this extra effort he was having to make due to her obvious inexperience would be worth it, but he probably should have gone for someone else that evening. She let out a few irritating giggles and gasps before events reached a natural end.

She was similar to the many before. The same could have happened with anyone. She wasn't anything special.

_Yeh right. Who do you think you're kidding_? He scolded himself. _She's so much more than any woman that's ever existed. _Rewind.

Despite the immense pleasure he was feeling he made his eyes stay open in order to take in every inch of her, every gesture and movement she made. He lifted up his hands to her glorious curls that felt like silk on his finger tips. He slid off the bejewelled headband that was so often her statement piece. Like the scarf habit of his own, it was her way of making her mark and standing out independently from the many cloned students of Constance. It had become the beacon that his eyes would look for when he was desperate for a glimpse of her to lift his spirit on a dull day of school. She ran her hands up his chest, over his thumping heart and onto his shoulders. Her nails dug into him as though she feared he might try and flee but he would never abandon this. Her delicate and feminine hands moved back down to his stomach and he felt like he would lose control as she teased her way beneath his waist band. "Not so fast gorgeous" he rasped as he pulled her hands back out, worried by the risk of a truly school boy ending to this passion.

He tore away her dressing gown and she helped him shrug out of his clothes whilst continuing to overwhelm his lips and mouth with her warm tongue. He tried to slowly work his hands up her warm and smooth thighs. It took all his will power not to just plunge his fingers into her heat. Her fingers had found the back of his neck and were caressing the skin and tugging naughtily at his hair. It felt like she was plugging into his brain, his soul, and taking complete control of him. His hands had reached her ass and he was desperate to rip away the soft lace knickers that provided the final barrier between them. He flipped her off him and rolled onto her, his fingers grabbing and tugging a handful of lace away from her. Inside of him he knew there was an endless pool of energy and desire to please her. As he finally pushed into her their bodies moulded into a rhythm so easily. Some of her purrs and gentle moans sounded like a woman far more mature than her 17 years. When they were followed by sweet gasps and seductive giggles he was reminded of her youth and innocence. When it came back to him that he was her first, that he was the only man in the world to have had her, he couldn't hold himself together another second longer. He woke slowly as she twisted in his arms. Her back was pressed into his chest, his legs were tucked up under hers and his arms held her close to him. As hazy twinkles cleared from his vision he realised the sun had risen across her bedroom. He slowly recalled the events of a Friday night that had begun with him alone in his suite and ended here. It was the first in a long time that was spent sober. It was the first time he hadn't cared for his own pleasure at all. It was the first time he'd spent the entire night with a woman in his arms. It was the first time he'd felt it. Love.


	2. Chapter 2: Extended version

Tonight was just like any other. A woman hooking on to his facade of attentiveness and then being reeled in by his witty and seductive conversation and subtle physical advances. The final landing was never difficult and often had been dead certain from the first moment of eye contact.

Here she was, the same as so many others before. Her childish brown curls swishing around as she straddled him on the bed. A silly headband failing to have any control, clearly just a lame accessory used to draw attention to her plain self. Her oddly small hands just followed the usual pathway. Up to his chest, grabbing his shoulders, running back down to his belt, a boring 'will she-won't she' as her fingers slide under his waist band but then out of it again and again.

She should put a bit more effort into kissing him effectively. He should not have to try to stay hard. His own hands performed the same show as so many times before. Politely starting on the back of her thighs just above the knee. Pretending every centimetre climbed towards her centre excited him more and more so that she would be encouraged. It didn't really. Her skin felt scratchy under his finger tips and the lace of her French knickers cheap once he reached them.

Now she was doing that thing at the base of his neck that women seemed to think he would enjoy. Tickling him a bit and tangling her finger tips into the hair there. If he had been looking for a head massage he would have gone somewhere authentic to ensure a decent experience.

He flipped her down into the mattress in an attempt to speed things along a bit. He could probably get out of here in the next 20 minutes if he took control now. He mentally referred to his extensive toolkit of moves and techniques to hurry things along. Hopefully this extra effort he was having to make due to her obvious inexperience would be worth it, but he probably should have targeted someone else that evening. She let out a few irritating giggles and gasps before events reached a natural end.

She was similar to the many before. The same could have happened with anyone. She wasn't anything special.

_Yeh right. Who do you think you're kidding_? He scolded himself. _She's so much more than any woman that's ever existed._

**Firstly**, this night had not started in a dimly lit New York City bar. He hadn't needed to sit in a booth portraying a dying hyena waiting for the vultures to start circling. It had started with a three worded text message "Want to play? B". She didn't need to initial it. She was one of the few females whose number he actually cared to store in his cell.

The moment he had read the words the butterflies in his stomach had fluttered to life. "Pick you up in 20" had been his response. He'd quickly shrugged out of his comfortable red onesie and noticed that he spent more time than usual selecting his outfit.

On the way to her penthouse on Fifth Avenue he considered how he might entertain her this evening and he wasn't just thinking about beneath the bed sheets or in the back of the limo. It had been two weeks since her 17th birthday and they had been enjoying each other's company a lot behind closed doors. Perhaps it was time to show her what else he had to offer. Dinner at any of the city's finest restaurants. Drinks in any of the most exclusive bars. Anything was a possibility on the Chuck Bass experience. He'd let her decide tonight.

A few minutes later he was tapping out a text to let her know he was waiting downstairs in the limo when Arthur opened the door. "Mr Bass the doorman has just informed me that Miss Waldorf would like you to meet her in the penthouse". "Very well then", Chuck responded with raised eyebrows as he slid out of the limo. Their recent trysts had rarely occurred at Blair's place. Partly due to the fear of Eleanor catching on and probably also Blair's lack of desire for him to officially be a notch on her, until recently, virginal bed post. He perfected the fit of his jacket in the elevator and prepared to charm Eleanor if she was present.

Blair wanted to slap her own hands to stop them from shaking as she straightened out her Marc Jacob's dress in front of her closet mirror. She had matched it with ivory stockings and an ivory lace knicker and bra set. A headband with a jewelled piece off-centre rested in her hair. She couldn't help but speculate over the type of place and type of girl she'd likely lured him away from on a Friday evening. _Would he be glad?  
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A spell of self confidence had been cast over her that night at Victrola and it had remained strong in the week that followed as Chuck Bass continued to expose the secret fire burning inside of her. In the past few days she had felt the spell wearing off. It had taken her 30 minutes of thumb twiddling to convince herself to text him tonight and now she felt sick with nerves. Perhaps this dress didn't do her hips any favours after all and her face had seemed kind of puffy today with no amount of make up contouring being able to fix it. She looked over her reflection from head to toe. _No. No way._ She couldn't handle him tonight after all.

"DOROTA!" she yelled. "Yes Miss Blair?" her faithful servant scurried into the closet as Blair began removing her outfit. "Call down and get a message to Chuck Bass when he arrives. I won't be able to see him this evening after all. I've had a sudden bout of food poisoning and feel incredibly unwell". "Miss Blair, Mr Chuck is already in foyer waiting for you" the maid said with concern. "Urrgghhh!" Blair let out a disgruntled moan. "Get rid of him!" "I try my best for you!" and the maid was gone.

Blair wrapped her dressing gown over her underwear clad body as she sulked down onto her bed. Chuck wouldn't be happy. But perhaps it was wise to make herself unavailable now and then, to play him a little. But she did feel a strong itch that she had no doubt he could scratch. "Urrgghhh!" She exclaimed again out loud at the stupidity of the situation and raised her hands over her face in frustration.

"Well well Waldorf! You really do appear to be in an uncomfortable state. Shall I ask the help to prepare a flat Coca Cola to sooth your system?" Her eyes shot up to see him leaning in the doorway with the light from the hallway catching on his sharp jaw line. The jaw she'd become far too fond of kissing, nibbling and licking during the short course of their affair. "Coca Cola belongs in a Brooklyn bar Bass. Besides, my digestive system is in good shape. It's a migraine that is ailing me. You were misinformed. It's the language barrier you see." The last thing she wanted him to be thinking about was her bowel movement! Why hadn't she thought of a more complimentary condition to have suddenly been overcome with? "You're free to go. I wouldn't want to hold you back any further from your usual Friday night fun and frolics." She forced a tight smile at him and hoped he couldn't see right through her.

"I see" Chuck accepted her change in medical circumstances without argument. "Well there is no way I can return to my previous activities of this evening now and I can't be seen returning to The Palace alone this early on a weekend. So shall I go and play piano to aid Dorota in her dusting or can I be of service here?" He took a few steps into the room. He'd sounded as smooth as he could but the excited little boy inside of him desperately wanted her to let him stay. Blair felt as though she was regaining some control of herself and the situation. And he was pinning her with those wanting dark eyes of his. _Did he want her?_

"Miss Blair. I bring some plain bread and water to help your stomach recover" Dorota winked at her as she entered the room with a tray and placed it on her desk. "Dorota, you've misunderstood me. Headache tablets would be more appropriate!" Blair widened her eyes dramatically at Dorota. "There are some in my bathroom already so forget it! I'm going to be recovering here for the rest of the evening so with that and my Mother being away you should take the rest of the night off. Chuck will be able to see himself out once we're finished talking". The maid didn't argue. "Thank you Miss Blair. Good night. I will check on you in the morning".

Chuck's spirits dropped slightly. He needed to start guiding the conversation to avoid Blair showing him the door. He couldn't work out what was with her tonight despite reading her so well in the past two weeks. "Well seeing as you're here Bass you won't mind fluffing up my pillows will you?" He took it as a command rather than a question. He walked towards the bed and reached for the pillows behind her. She watched him realising he'd never fluffed pillows before. He caught a whiff of her delicious scent as he leant behind her and it assaulted his senses more than he expected. "How's that?" he asked, trying to hide the fact he was flustered. His bedside manner was usually so much slicker. "Perfect. Now there's only one more thing I need to make me feel better" she said as she their eyes met. "And is it something I can provide?" He responded, leaning down towards her and gently moving a stray whisp of hair from over her eye. "It is." She reached for his lapel. _I'm back in the game _he thought. "I need...Audrey". _Point to Waldorf._

**Second**, Chuck Bass had never spent so long lying on a female's bed without touching her. He'd followed Blair's wishes and set up the movie. Half of him felt sickened by what those damn butterflies were leading him to do and apart from some accidental brushing of feet/legs/shoulders they hadn't touched each other. But the spark from every accidental touch had rocketed through his whole body.

She sighed contentedly as the credits began to roll and shimmied down the bed far enough to be able to use her foot to close the laptop that was resting on the chest at the foot of the bed. She'd felt secretly pleased that he hadn't abandoned her despite her unwelcoming attitude earlier. It had boosted her confidence to see him be attentive and, well, caring when he arrived. They'd got a few minutes into Breakfast at Tiffany's before she made her next play, rearranging her legs subtly so that slightly more of them were on show. At regular intervals she'd needed to wriggle or readjust slightly, making sure that any movement would create a touch between them. Each time something tingled through her that she had never felt with Nate. Probably pure fear because a Bass was in close proximity.

She turned her head to glance over at him and found absolutely nothing to be afraid of. Chuck Bass was sleeping like a baby. The contrast on someone who was so often somewhat agitated and constantly on alert was blinding. He looked adorably handsome. His breathing was regular and gentle. His eyes and cheeks were relaxed. He'd titled his head up slightly and his defined jaw held everything in place. _That jaw._ She felt her own butterflies flurry inside her. Without much thought she raised her finger tips to it and stroked lightly up and down. She moved her face closer to his.

Chuck woke feeling the gentle caress on his face. He slowly opened his eyes and met a beautifully brown pair staring at his own. Before she could pull back he raised his hand to her face, holding her in place. He leaned in, closing the space between their mouths to just millimetres. "Feeling better now Waldorf?" _God he wanted her_. He didn't give her a chance to respond. He touched his lips to hers, allowing the tip of his tongue to glide gently across her. He waited what felt like an eternity before she responded and kissed him back.

They continued this to and fro-ing for a long time. It was simple but blissful. He took one of her hands in each of his own and continued to caress her lips with his own. There was no hurry. He would stay like this for days if she let him. She felt more sexy, sensuos and wanted than she ever had before in her life. Just two hours of his company had fixed her earlier confidence wobble. She needed him and was sure he needed her too so she lifted herself up and over him, positioning her knees on either side of him.

Despite the immense pleasure he was feeling he made his eyes stay open in order to take in every inch of her, every gesture and movement she made. He lifted up his hands to her glorious curls that felt like silk on his finger tips. He slid off the bejewelled headband that was so often her statement piece. Like the scarf habit of his own, it was her way of making her mark and standing out independently from the many cloned students of Constance. It had become the beacon that his eyes would look for when he was desperate for a glimpse of her to lift his spirit on a dull day of school.

She ran her hands up his chest, over his thumping heart and onto his shoulders. Her nails dug into him as though she feared he might try and flee but he would never abandon this. Her delicate and feminine hands moved back down to his stomach and he felt like he would lose control as she teased her way beneath his waist band. "Not so fast gorgeous" he rasped as he pulled her hands back out, worried by the risk of a truly school boy ending to this passion. He tore away her dressing gown and she helped him shrug out of his clothes whilst continuing to overwhelm his lips and mouth with her warm tongue.

He tried to slowly work his hands up her warm and smooth thighs. It took all his will power not to just plunge his fingers into her heat. Her fingers had found the back of his neck and were caressing the skin and tugging naughtily at his hair. It felt like she was plugging into his brain, his soul, and taking complete control of him. His hands had reached her ass and he was desperate to rip away the soft lace knickers that provided the final barrier between them. He flipped her off him and rolled onto her, his fingers grabbing and tugging a handful of white lace away from her.

Inside of him he knew there was an endless pool of energy and desire to please her. As he finally pushed into her their bodies moulded into a rhythm so easily. Some of her purrs and gentle moans sounded like a woman far more mature than her 17 years. When they were followed by sweet gasps and seductive giggles he was reminded of her youth and innocence. When it came back to him that he was her first, that he was the only man in the world to have had her, he couldn't hold himself together another second longer.

**Third**, he was still in the same place 8 hours later. He woke slowly as she twisted in his arms. Her back was pressed into his chest, his legs were tucked up under hers and his arms held her close to him. As hazy twinkles cleared from his vision he realised the sun had risen across her bedroom. He slowly recalled the events of a Friday night that had begun with him alone in his suite and ended here. It was the first in a long time that was spent sober. It was the first time he hadn't cared for his own pleasure at all. It was the first time he'd spent the entire night with a woman in his arms. It was the first time he'd felt it. _Love._


End file.
